Italy failed to qualify for the last eight of Euro 2004 despite beating Group C whipping boys Bulgaria. Martin Petrov fired Bulgaria ahead from a controversial penalty on the stroke of half-time.
Simone Perrotta pulled Italy level within two minutes of the restart after Antonio Cassano's shot hit the bar.
Cassano superbly converted a low cross for Italy's injury time winner but Sweden's 2-2 draw with Denmark rendered their victory academic.
Driving rain in Guimaraes presented players with difficult conditions underfoot.
Andrea Pirlo's raking pass picked out Alessandro del Piero but the Bulgarians gave an early hint of their intent not to go out tamely by swarming round the Italian captain and crowding him out.
Petrov showed their attacking intentions by showing Christian Panucci a clean set of heels but Italy should have gone ahead on 13 minutes.
Cassano picked out Gianluca Zambrotta at the far post, and his thumping close range volley was brilliantly saved by Zdravko Zdravkov, who then watched gratefully as Del Piero stabbed the loose ball wide of the gaping target. Italy's frustration at being unable to fashion an early opening showed when Petrov again skinned Panucci, only for Perrotta to crudely end his run.
Fine defending at either end kept the game scoreless, with Marco Materazzi bravely throwing himself in front of Dimitar Berbatov's piledriver and when play swept to the other end Zlatomir Zagorcic timed his challenge to perfection as Del Piero cocked the trigger.
With half-time beckoning, Italy were facing a mountain to climb as Bulgaria took the lead in controversial fashion.
 | KEY MOMENTS 13 mins: Del Piero stabs wide of an open goal 45 mins: Petrov converts a controversial penalty 47 mins: Perotta reacts to fire Italy level 91 mins: Cassano fires Italy's winner to no avail |
Materazzi was harshly penalised for a foul on Berbatov and Petrov confidently rapped home their first goal in the competition from the penalty spot.
But within two minutes of the restart, Italy were back in business.
Gianluca Zambrotta pulled the ball back from the bye-line for Cassano to crack a shot against the underside of the bar and when Zdravkov failed to gather the rebound Perrotta reacted first to prod home the loose ball.
Italy still needed goals and Pirlo curled a free-kick just over with Zdravkov backpedalling desperately.
Coach Giovanni Trapattoni threw Christian Vieri into the fray and the Inter striker mis-timed his header in front of goal and in the ensuing scramble Del Piero had a shot blocked. The missed chance count continued to rise for Italy and Cassano failed to test Zdravkov after Del Piero picked him out at the far post.
Italy poured forward and Vieri rose highest at a corner to bullet a header inches wide before referee Valentin Ivanov turned down what looked a certain penalty when Cassano was felled by Daniel Borimirov's poorly timed tackle.
Zambrotta then saw his shot deflected wide with Zdravkov stranded.
Gianluigi Buffon had been a spectator but on 85 minutes produced a brilliant save to keep out Berbatov's free-kick. The game ended in torment for Italy as Cassano brilliantly converted Del Piero's low cross.
Italian joy at what they thought was the goal to put them through was instantly cut short as news filtered through of Denmark's draw with Sweden.
Italy: Buffon, Panucci, Nesta, Materazzi (Di Vaio 83), Zambrotta, Fiore, Pirlo, Perrotta (Oddo 68), Cassano, Del Piero, Corradi (Vieri 53).
Subs Not Used: Toldo, Peruzzi, Zanetti, Ferrari, Favalli, Camoranesi. Booked: Materazzi.
Bulgaria: Zdravkov, Borimirov, Pazhin (Kotev 64), Zagorchich, Stoyanov, Milen Petkov, Yankovich (Bojinov 45), Hristov (Dimitrov 79), Lazarov, Martin Petrov, Berbatov
. Subs Not Used: Kolev, Ivankov, Ivanov, Ivaylo Petkov, Peev, Chilikov, Manchev.
Booked: Martin Petrov, Bojinov, Stoyanov, Lazarov.
Attendance: 29,643.
Referee: Valentin Ivanov (Russia).
| OFFICIAL STATS BY UEFA |
| Category | Italy | Bulgaria |
| Total shots | 25 | 10 |
| Shots on target | 13 | 5 |
| Possession | 52% | 48% |
| Corners won | 6 | 3 |
| Fouls committed | 13 | 20 |
| Offsides | 11 | 2 |
| Bookings | 1 | 4 |
| Sent Off | 0 | 0 |
TRIVIA
Euro 2004 marks the second time in six European Championship participations Italy have failed to negotiate the group phase. The other occasion on which they crashed out was 1996. Italy are still to score more than two goals in a European Championship match, having appeared in 23 encounters in this competition. They have not lost in their last eight competitive matches. Their last defeat came on 16 October 2002 in their European Championship qualification match in Wales when they went down 2-1. Bulgaria's Valeri Bojinov became the second youngest player ever to appear in a European Championship match. Bojinov is assured of being the youngest player at Euro 2004, which means Belgium's Enzo Scifo will hold on to the championship record for at least another four years. The sequence of at least one of the finalists from the previous European Championship exiting in the group phase of the next tournament is now 20 years and running. 
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